Asarone

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Asarone
α-Asarone
β-Asarone
Names
IUPAC names
1,2,4-Trimethoxy-5-[(E)-prop-1-enyl]benzene (α)
1,2,4-Trimethoxy-5-[(Z)-prop-1-enyl]benzene (β)
Other names
alpha-Azaron
cis-Isoelemicin
2,4,5-Trimethoxyphenyl-2-propene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
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UNII
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  • InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5+ checkY
    Key: RKFAZBXYICVSKP-AATRIKPKSA-N checkY
  • InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5- checkY
    Key: RKFAZBXYICVSKP-WAYWQWQTSA-N checkY
  • (α): O(c1cc(c(OC)cc1OC)/C=C/C)C
  • (β): C/C=C\c1cc(c(cc1OC)OC)OC
Properties
C12H16O3
Molar mass 208.257 g·mol−1
Appearance Colorless solid
Density α: 1.028 g/cm−3 [1]
Melting point 62 to 63 °C (144 to 145 °F; 335 to 336 K)[2] (α)
Boiling point 296 °C (565 °F; 569 K)[2] (α)
Insoluble
−131.4·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Asarone is chemical compound of the phenylpropanoid class found in certain plants such as Acorus and Asarum.[2] There are two isomers, α (or trans) and β (or cis).[3] As a volatile fragrance oil, it is used in killing pests and bacteria.[4]

Pharmacology

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The main clinical symptom of asarone is prolonged vomiting that sometimes lasted more than 15 hours. Asarone is not metabolized to trimethoxyamphetamine as has been claimed by online vendors.[5]

The Council of Europe Committee of Experts on Flavouring Substances concluded that β-asarone is clearly carcinogenic[6] and has proposed limits for its concentration in flavorings such as bitters made from Acorus calamus (sweet flag).[7]

β-Asarone exhibits anti-fungal activity by inhibiting ergosterol biosynthesis in Aspergillus niger.[8] However, the toxicity and carcinogenicity of asarone means that it may be difficult to develop any practical medication based on it.[9]

See also

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Notes and references

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  1. ^ Data for α-Asarone at ChemSpider
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  3. ^ Beta asarone has CAS# 5273-86-9
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  9. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
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